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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Eric Hacker | 49 | 2017-2022 | |
| 2 | Zack Trageton# | 38 | 2020-2026 | |
| 3 | William Cuevas# | 35 | 2016-2021 | |
| 4 | Logan Darnell | 32 | 2013-2024 | |
| 4 | Mark Leiter Jr.# | 32 | 2015-2021 | |
| 6 | Tyler Rogers# | 30 | 2015-2017 | |
| 7 | Jordan Guerrero# | 29 | 2017-2026 | |
| 7 | Eric Jokisch# | 29 | 2024-2025 | |
| 9 | Branden Kline | 28 | 2014-2016 | |
| 9 | Chad Kuhl# | 28 | 2023-2026 | |
| 11 | Dillon Peters# | 27 | 2023-2026 | |
| 12 | Conor Harber | 26 | 2016-2021 | |
| 13 | Domingo Acevedo# | 25 | 2016-2018 | |
| 13 | Pearson McMahan# | 25 | 2023-2025 | |
| 15 | Patrick Francescon | 24 | 2013-2015 | |
| 15 | Deivi Garcia# | 24 | 2022-2026 | |
| 15 | Jacob Lee | 24 | 2014-2016 | |
| 15 | Zac Lowther# | 24 | 2024-2026 | |
| 19 | Simeon Woods Richardson# | 23 | 2020-2024 | |
| 20 | John Cornely | 22 | 2013-2017 | |
| 20 | Jimmy Gillheeney | 22 | 2013-2015 | |
| 20 | Jay Jackson | 22 | 2013-2021 | |
| 20 | James Marvel | 22 | 2021-2023 | |
| 20 | Travis Radke | 22 | 2016-2019 | |
| 25 | Justin Ferrell | 21 | 2018-2019 | |
| 25 | Jake Jewell# | 21 | 2017-2025 | |
| 25 | Pierce Johnson# | 21 | 2014-2015 | |
| 25 | Ryan O'Rourke | 21 | 2014-2022 | |
| 25 | Tyler Phillips# | 21 | 2019-2020 | |
| 25 | Tyler Pill | 21 | 2014-2019 | |
| 25 | Logan Rinehart# | 21 | 2021-2024 | |
| 25 | Tayler Scott# | 21 | 2016-2019 | |
| 25 | Tanner Tully# | 21 | 2018-2021 | |
| 34 | Randy Bell# | 20 | 2019-2025 | |
| 34 | Casey Bloomquist | 20 | 2018-2023 | |
| 34 | Luis Diaz | 20 | 2015-2017 | |
| 34 | Dylan Floro# | 20 | 2014-2016 | |
| 34 | Matt Purke | 20 | 2014-2017 | |
| 39 | Matt Allan# | 19 | 2021-2026 | |
| 39 | Ryan Carpenter# | 19 | 2013-2025 | |
| 39 | Raudel Lazo | 19 | 2014-2017 | |
| 39 | Jake Lyons# | 19 | 2020-2025 | |
| 39 | Zachary Nuding | 19 | 2014-2016 | |
| 39 | Brady Puckett# | 19 | 2019-2025 | |
| 39 | Tommy Sommer# | 19 | 2023-2025 | |
| 39 | Tyler Stuart# | 19 | 2024-2026 | |
| 39 | Cory Taylor | 19 | 2017-2020 | |
| 48 | Edgar Arredondo# | 18 | 2020-2026 | |
| 48 | Beau Burrows# | 18 | 2018-2025 | |
| 48 | Frank Duncan | 18 | 2017-2021 | |
| 48 | Tyler Glasnow# | 18 | 2014-2015 | |
| 48 | David Hill | 18 | 2017-2019 | |
| 48 | Casey Kelly# | 18 | 2023-2026 | |
| 48 | Christopher Kirsch | 18 | 2016-2017 | |
| 48 | Marcelo Martinez# | 18 | 2020-2021 | |
| 48 | Luis Mateo | 18 | 2014-2017 | |
| 48 | Griffin McLarty# | 18 | 2022-2026 | |
| 48 | Ryan Murphy# | 18 | 2024-2026 | |
| 48 | Matthew Tracy | 18 | 2013-2014 | |
| 48 | Julio Urias# | 18 | 2015-2016 | |
| 61 | Luke Albright# | 17 | 2023-2025 | |
| 61 | Sam Bachman# | 17 | 2022-2024 | |
| 61 | Derek Casey# | 17 | 2022-2025 | |
| 61 | Brock Dykxhoorn | 17 | 2017-2023 | |
| 61 | Blayne Enlow# | 17 | 2020-2025 | |
| 61 | Ryan Forcucci# | 17 | 2025-2026 | |
| 61 | Chris Jensen | 17 | 2016-2018 | |
| 61 | Bud Jeter | 17 | 2015-2020 | |
| 61 | Karl Kauffmann# | 17 | 2022-2026 | |
| 61 | Brett Kennedy# | 17 | 2018-2025 | |
| 61 | Gennison Reyes | 17 | 2015-2018 | |
| 61 | Austin Ross | 17 | 2013-2014 | |
| 61 | Jose Urena# | 17 | 2013-2019 | |
| 61 | Cole Winn# | 17 | 2023-2024 | |
| 75 | Brady Aiken | 16 | 2018-2019 | |
| 75 | D.J. Baxendale | 16 | 2016-2017 | |
| 75 | Jack Carey# | 16 | 2023-2025 | |
| 75 | Odrisamer Despaigne# | 16 | 2023-2024 | |
| 75 | Drake Fellows# | 16 | 2025-2026 | |
| 75 | Alec Gamboa# | 16 | 2023-2026 | |
| 75 | Ryan Lillie | 16 | 2020-2021 | |
| 75 | Brett McKinney | 16 | 2016-2017 | |
| 75 | Nick Raquet# | 16 | 2018-2019 | |
| 75 | James Reeves | 16 | 2019-2023 | |
| 75 | Luis Reyes# | 16 | 2020-2025 | |
| 75 | Kraig Sitton | 16 | 2015-2017 | |
| 75 | Giovanni Soto | 16 | 2013-2014 | |
| 75 | Garrett Stallings# | 16 | 2023-2026 | |
| 89 | Osvaldo Berrios# | 15 | 2019-2026 | |
| 89 | David Buchanan# | 15 | 2023-2026 | |
| 89 | Trevor Clifton# | 15 | 2018-2019 | |
| 89 | Brett Graves | 15 | 2017-2021 | |
| 89 | Rainy Lara | 15 | 2014-2017 | |
| 89 | Reid Love | 15 | 2018-2023 | |
| 89 | Kevin McGowan | 15 | 2018-2020 | |
| 89 | Trevor Megill# | 15 | 2019-2021 | |
| 89 | Dane Myers# | 15 | 2021-2023 | |
| 89 | Justin Nicolino | 15 | 2014-2014 | |
| 89 | Henry Owens | 15 | 2013-2014 | |
| 89 | Emilio Pagan# | 15 | 2016-2018 |
